The Development of Mercury Photosensitized Reactions for Functionalizing Unactivated C - H Bonds in Organic Compounds

The weakest C - H bonds of a variety of organic compounds can be selectively homolyzed and the resulting carboncentered radicals dimerized by mercury photosensitized reactions. Cross-dimerizations give a variety of interesting multifunctional compounds. In certain cases, the radicals can be trapped by sulfurdioxide, carbon monoxide or oxygen. The addition of hydrogen produces hydrogen atoms which are more selective abstractors and allow the method to be extended to a wider variety of compounds, e.g., esters, carboxylic acids, alkenes, ketones, fluorocarbons, amines, and amides. The procedure gives multigram quantities of products in a simple reflux apparatus under ambient pressure and modest temperatures.